GOSSIP GIRL [Book 3] Recap: “Ridiculously Flirtatious” Serena and Horny Chuck (Part 1)

[The original CW Gossip Girl series was called “Mind-blowingly inappropriate.” by the Parents Television Council, “Very bad for you." by the San Diego Union-Tribune, and “A nasty piece of work.” by the New York Post. However, I would argue that the young adult novel series is inarguably more salacious. I plan to recap books 1-8, 13, and 14, which were written by Cecily von Ziegesar and are based on Ziegesar's experiences at The Nightingale-Bamford School, an Upper East Side all-girls prep school.]

Serena

In Gossip Girl: All I Want is Everything (Book 3), Ziegesar described 17-year-old Serena as having a “perfectly chiseled face, deep blue eyes, [and a] long, lithe body”. And four paragraphs in on page 3, Ziegesar reminded readers: “After all, she [i.e., Serena] and Nate had lost their virginity together behind Blair’s back the summer after tenth grade.” Talk about getting right to the (salacious) point!

After Flow, the “former model and gorgeous lead singer and guitar player, whose band, 45, [had] just won the MTV Music Award for best album”, performed at the Black-and-White Ball, Serena, with her “beautiful blond head”, sat on Flow’s lap in the backseat of his limo.

Ziegesar wrote that Serena was being “ridiculously flirtatious” in the limo, because “she loved the way Flow’s dark brown hair curled around his temples”, she loved “his golden bronze skin”, and, interestingly, Serena loved “how long and delicate looking his fingers were.” Consequently:

“Serena dipped her fingers in her champagne glass and then put them in her mouth [...]”

Flow kept on staring at her.

Serena giggled. “Stop it.”

“Ooh, baby,” Chuck said obnoxiously, sucking on his joint. “Somebody is getting some tonight!”

Subsequently, Gossip Girl posted that Serena and Flow “were seen entering the Tribeca Star—to get a room, perchance? Naughty, naughty—”

During Christmas break, Serena and Blair went to St. Barts, where they stayed at the "exclusive Isle de la Paix resort”. (Blair’s family met them there.) At the resort, Ziegesar wrote that Serena wore outfits like a “tiny white denim Agnès B. miniskirt [that] barely covered the tops of her legs” and “red velvet Juicy Couture sweatpants and a tiny little T-shirt with a picture of a snowman on it.” However, Ziegesar did not share that Serena’s sweatpants read Juicy Couture on her derrière.

Before Serena and Blair left for St. Barts, it was posted on Gossip Girl that they were seen “leaving the J. Sisters Salon after their pre St. Bart's bikini waxes.” Consequently, Gossip Girl wrote: “Looks like it’s going to be hotter than hot down there!”

Back in Manhattan at Serena’s New Year’s Eve party, where there were “torches smoldering in the corners, and the dance floor was made of real green grass. [And] [t]he bartenders were wearing skimpy crocheted bikinis”, Serena wore “a Missoni string bikini top, black velvet short shorts, and long, dangly diamond earrings”.

Not to be eclipsed, Blair wore “a purple suede Dior micro-miniskirt, a black satin Chloé camisole, and black fishnet tights.” After Blair “took a large gulp” of her Ketel One and tonic and a “deep drag” of her Merit Ultra Lite, she saw schoolgirl “Serena bump butts with two dark-haired men in their twenties wearing matching navy blue sailor suits, who looked like twins.” (Note: Ziegesar did not disclose Flow’s age, but it’s safe to infer that he was in his twenties too.)

And speaking of Gossip Girl and New Year’s Eve, Gossip Girl encouraged Upper East Side schoolgirls that to have the “rockingest New Year’s Eve ever”, they should get some action by making out with strangers. Ziegesar slash Gossip Girl posted:

How to have the rockingest New Year’s Eve ever

Two words of advice:

1) Stick with me. I know where the action is.

2) Kiss people. Tonight at midnight is the only time in the entire year when you have an open invitation to kiss completely random people without any explanation at all. So go for it!

Chuck

Ziegesar described Chuck as “handsome in a dark, after-shave commercial sort of way” and “also the horniest boy in all of New York City.”

Rhetorical question: Should Chuck’s hyperbolic horniness be an excuse for him to molest a Blacked-out Serena in a hotel suite and/or force (14-year-old) Jenny to undress in the bathroom at The Met? Ziegesar wrote:

Chuck was handsome in a dark, after-shave commercial sort of way. He was also the horniest boy in all of New York City. He had tried to molest Serena when she was passed out drunk in his family’s Tribeca Star Hotel suite in October, and he had almost gotten little Jenny Humphrey to take her dress off for him in the ladies’ room at the Kiss on the Lips party that same week.

Only a month later at Serena’s New Year’s Eve party, Blair discovered Chuck on the deck “furiously eating olives, smoking cigarettes, gulping Veuve Clicquot” while “he was looking for someone to give him a blow job while the fireworks went off.”

Unsurprisingly, Chuck, who Ziegesar further described as “a serious asshole, especially when it came to girls”, kissed Blair on the lips, without her consent, and he “slowly slid his hand down her back and over her ass”, without her consent. Ziegesar wrote:

Blair wasn’t surprised when Chuck Bass found her standing out on the deck, furiously eating olives, smoking cigarettes, gulping Veuve Clicquot, and freezing her ass off. It was just before midnight, and knowing Chuck, he was looking for someone to give him a blow job while the fireworks went off.

“Happy New Year, Blair.” Chuck walked right up and kissed her on the lips. There was an olive pit in her mouth, but he didn’t seem to mind.

Chuck put his arm around her and then slowly slid his hand down her back and over her ass.

Nonetheless, after Chuck asked rhetorically, “You know what’s the best way to ring in the new year?”, despite Chuck’s infamous reputation, Blair suggested that he ring in the new year in the best way with not one but two schoolgirls: Kati, a strawberry-blond, and Isabel, the daughter of a well-known actor. Ziegesar wrote:

“You know what’s the best way to ring in the new year?”

She pulled away and pointed through the glass doors to where Kati and Isabel were standing on a little table holding each other’s hands and counting down the new year.

“Those two have always been totally in love with you,” Blair declared, trying to keep a straight face. “If you want to ‘ring in the new year’ with someone, why don’t you ask them?”

Chuck grinned at her. “Really?”

She nodded. “Go ahead, I’m—” But before she could even finish her sentence, Chuck ducked back inside and grabbed the two girls in a group hug.

“Four! Three! Two!”

Of Chuck and Kati, recall I wrote that in the book 1 recap:

[...] Ziegesar described Chuck as “the horniest boy” in the friend group. So much so that after hiding in the guest room closet, Chuck crawled into bed with Kati Farkas whom was “so drunk she kept throwing up in her sleep”. Shockingly, Kati’s vomit on the sheets didn’t deter Chuck, because when it came to schoolgirls, “[h]e was completely unshakeable”.

Big Boobs Jenny and Fun Slut Vanessa | GOSSIP GIRL [Book 2] Recap (Part 2)

Gossip Girl: You Know You Love Me (Book 2): Jenny, Vanessa and Chuck

[The original CW Gossip Girl series was called “Mind-blowingly inappropriate.” by the Parents Television Council, “Very bad for you." by the San Diego Union-Tribune, and “A nasty piece of work.” by the New York Post. However, I would argue that the young adult novel series is inarguably more salacious. I plan to recap books 1-8, 13, and 14, which were written by Cecily von Ziegesar and are based on Ziegesar's experiences at The Nightingale-Bamford School, an Upper East Side all-girls prep school.]

Jenny

As you may recall from book 2 part 1, Jenny is a 14-year-old “lowly ninth-grader” at Constance Billard School for Girls, which is a “small, elite, all-girls school on East Ninety-third Street”, where uniforms are required. And you may recall that Ziegesar wrote that during foreplay with Blair, Nate’s erection “stuck out, tentlike” in his “red-and-white checked boxers”. Interestingly, likewise, Ziegesar wrote that Jenny’s “enormous” “boobs” caused her “pink nightgown” to form a “tentlike triangle”. In terms of Jenny, Ziegesar penned: 

She stood in front of the mirror holding her breath and pushing her stomach out as far as it would go. It still didn’t stick out as far as her boobs, which were enormous for a ninth-grader. Her pink nightgown fell in a tentlike triangle from her breasts to her knees [...] 

“Freak,” Jenny Humphrey whispered to her reflection.

(Note: Recall that in book 1, Ziegesar referred to Jenny’s “boobs” at least nine times. For instance, in book 1, Ziegesar wrote that Jenny’s “boobs” were: “[...] incredibly huge. At fourteen, she was a 34D.")

Consequently, when Jenny met Nate at “the edge of Sheep Meadow”, Nate, “tanned” with “dark honey-gold” hair, immediately noticed Jenny’s “huge” chest. Ziegesar wrote:

She reached the edge of Sheep Meadow and stepped onto the grass.

Jenny looked up. [Nate] […] the golden boy, standing only thirty feet away, hands on his hips, his green eyes sparkling. His cheeks were flushed pink and his forehead was beaded with sweat. Jenny wanted to taste it.

 

Nate noticed Jenny’s chest. Man, was it ever huge. He couldn’t let her get away, not without Jeremy and the other guys getting a chance to check her out.

That’s correct. Per Ziegesar, Jenny wanted to taste Nate’s sweat. (LOL) And Nate wanted the other seniors to check out Jenny’s huge chest. 

After mingling in Central Park, Nate took Jenny to his bedroom in his Upper East Side (triplex) townhouse, which had red marble floors and famous artists like Renoir, Sargent, and Picasso “on every wall”. 

After Nate said, “Let’s go upstairs,” Jenny followed Nate to his bedroom, which had an “antique sleigh bed” and an “ultramodern, ultracool desk with a wafer-thin laptop sitting on it”. Without being asked, Jenny sat “nervously on the edge of the bed”, where she searched Nate’s “emerald green” eyes and shared,  “I’m only fourteen”. What was 17-year-old Nate’s response? Ziegesar wrote:

Nate reached up and touched her curly brown hair, combing it ever so gently with his fingers. Then he put his hand down again. “I know,” he said. “It’s okay.”

Although, Ziegesar left it flirtatiously ambiguous, based on forthcoming chapters, readers can safely infer that Nate did not have sex Jenny the first time she sat on his antique bed. 

In the Gossip Girl post “EVERYBODY’S DOING IT”, Gossip Girl was asked about her thoughts on “older boys dating young girls”. Gossip Girl opined that “a college senior dating a high school sophomore” is a bit of a problem, that “a high school senior dating a college freshman” is “okay”, but a 12th grader dating a 9th grader is “pushing it”; however, in what most people, I would imagine, would consider to be a counterintuitive and controversial stance, Gossip Girl opined that age-gap affairs “work better” when the “the girl is the younger one”. Ziegesar wrote:

Dear GG,

What do you think about older boys dating younger girls?

—Sneaky

      

Dear Sneaky,

It definitely depends on the age difference and the circumstances. For instance, if you were a college senior dating a high school sophomore I would say you had a bit of a Woody Allen-Soon Yi Previn problem. If you were a high school senior dating a college freshman, that would be okay. A high school senior dating a high school freshman is pushing it. It seems to work better when the girl is the younger one, mainly because we mature much faster—in all ways.

—GG

Notes: 

1. Ziegesar’s Woody Allen-Soon Yi Previn reference is about Woody Allen’s affair with Soon Yi Previn, which began when Soon Yi was Woody’s teen stepdaughter. For further information about Woody and Soon Yi’s affair and eventual age-gap marriage, reference the Substack piece “The Same Thing Only Different: Nympholepsy in Woody Allen’s Art and Affairs”

2. In a (somewhat) related note, in the FAMILY MATTERS post, Gossip Girl encouraged what she called “innocent flirting with your stepbrother-to-be”, because it “isn’t sick or illegal”. And she described what some would refer to as incest as “pretty fun and pretty damned convenient”; especially “if you live in the same house!” 

Woody Allen and Soon Yi Previn

One reason that readers may infer that Nate and Jenny did not have sex (yet) is that after Jenny met Nate on the steps of The Met, she thought: “Oh my God, [...] He’s about to kiss me.” He didn’t. The arrival of Nate’s friends (temporarily) prevented Jenny from getting what she so desperately desired.  

By this point in book 2, readers are up to about ten references to Jenny’s boobs. [I lost count.] Unsurprisingly, the count continues to rise up until the end of book 2. For example, after Jenny joined Nate and his friends on The Great Lawn, her “big boobs’ were spotted by none other than Dan, Jenny’s brother. Of Dan, Ziegesar wrote:

Puffing away, he stared across the grass. A short girl with big boobs and curly brown hair was playing soccer with four boys he recognized only vaguely. It was his sister, Jenny. Since when did she hang out in the park with those boring, preppy, Upper East Side assholes?

Recall from book 1 that Vanessa, another Constance schoolgirl, was in an age-gap relationship with a Brooklyn bartender. Does that make it less surprising that, over hummus and hot chocolate, Vanessa encouragingly referenced Jenny’s “rack”? Ziegesar wrote:

They walked to a café that specialized in Middle Eastern food and ordered hummus and hot chocolate.

“So, Jennifer. With a rack like that, how come you don’t have like, seven boyfriends?” Vanessa said, pointing directly at Jenny’s chest. 

Hummus and hot chocolate?! Seven boyfriends?! 

Recollect that Dan referenced his sister’s boobs in book 1. For example, Ziegesar wrote in book 1 that even Dan “could not deny” that his sister’s “boobs were really huge.” However, it turns out that Dan referenced his sister’s boobs in book 2 two times! The second time happened at the St. Claire Hotel during Eleanor and Cyrus’ wedding reception, where Ziegesar wrote that Dan recognized his sister’s “enormous cleavage”. Ziegesar wrote:

Dan slipped into a seat at the end of the St. Claire Hotel bar and ordered a double scotch on the rocks. With trembling hands he pulled a Camel out of his coat pocket and lit it.

Dan’s chest convulsed in a sob and he slumped forward, resting his forehead against the edge of his glass. Out of the corner of his eye, he saw a familiar shock of curly brown hair, the enormous cleavage, the tiny figure.

His sister.

And next to her, with his hands all over her enormous cleavage and tiny figure was that rich bastard, Nate.

Once again, Ziegesar left it flirtatiously ambiguous about what happened between Jenny and Nate in Nate’s bedroom; however, readers learned later that they did not kiss on that occasion, because Ziegesar wrote that the first time Jenny and Nate kissed was while they: “were sitting beside the boat pond in Central Park,” where “Nate pulled her toward him. They both kept their eyes open, smiling as they kissed.” (Note: “Jenny had [previously only] kissed two boys during a kissing game at a party once [...]”) 

However, later in book 2, Gossip Girl gossiped on the NOBODY DOES IT BETTER post that: “Word has it N and J have been hooking up after school every day. Poor B[lair].” Interestingly, in book 1, Ziegesar wrote that Blair and Nate “had done everything but” have actual sex. Is that what Ziegesar is implying Nate and Jenny did every day after school?

Vanessa

In book 2, readers learned more about Clark, Vanessa’s 22-year-old boyfriend. (Recall that Gossip Girl posted that “a high school senior dating a college freshman” is “okay”. But at 22, Clark would be more like a college senior.) Ziegesar penned that Clark, a bartender at The Five and Dime, a “dimly lit” bar in Williamsburg, had “red sideburns and beautiful gray eyes”. (Note: Per Google, someone with red hair and grey eyes is extremely rare and appears in less than 1% of the entire human population.)

Despite the fact that Vanessa, who dreamed of being a film major at  NYU, was still a (prep) schoolgirl who was sitting in a bar, Clark wasn’t shy about openly expressing his age-gap desires. For example, Clark “ran his fingers through Vanessa’s short-cropped black hair” and “blew her a kiss”. Likewise, Vanessa wasn’t shy about openly expressing her desire for an older boyfriend. Ziegesar wrote:

Clark came over and ran his fingers through Vanessa’s short-cropped black hair.

Clark was the bartender at The Five and Dime [...] Clark was twenty-two. He had red sideburns and beautiful gray eyes

[Vanessa] watched Clark’s butt as he bent over to stock the bar fridge with more bottled beer.

“Hey boyfriend,” she yelled at him. “I’m lonely.”

Clark looked over his shoulder and blew her a kiss.

Thank God for Clark, Vanessa thought.

However, because it was “kind of fun to be such a slut”, Vanessa’s age-gap affair with Clark didn’t stop her from flirting with Dan. For example, during the wedding reception at the St. Claire Hotel bar, Vanessa kissed Dan on his “quivering lips”. Ziegesar wrote:

Vanessa picked a ball of lint off her fishnets and flicked it onto the bar floor. She couldn’t believe she was actually flirting with Dan. She hadn’t even broken up with Clark yet! But it was kind of fun to be such a slut.

She leaned forward and kissed Dan on his quivering lips. “Right,” she said, her mouth still full of nuts.

Gossip Girl

Interestingly, in the Vanity Fair piece “‘Gossip Girl Was Me’: Cecily von Ziegesar Talks Manhattan vs. Cobble Hill” (2020), Ziegesar related that she was, in fact, Gossip Girl. Ziegesar said, “Gossip Girl wasn’t Dan in the books. She was the omniscient narrator. Gossip Girl was me,” which (some) feminists [parents] may find interesting when one considers that Ziegesar slash Gossip Girl encouraged schoolgirls to “break out those credit cards and hit Bendel’s and Barneys for some [...] sexy fishnet tights, [and] little wool skirts”. Not only did Ziegesar write that bulimic Blair vomited her quenelle, but Gossip Girl encouraged: “The way to any girl’s heart is to tell her she looks tiny. Girls kill to be tiny.” And what was Ziegesar slash Gossip Girl’s advice on how to handle “senior stress management”? Materialism, alcoholism, and (teen) sex. Ziegesar/Gossip Girl posted: 

It’s time to break out those credit cards and hit Bendel’s and Barneys for some cool new boots, sexy fishnet tights, little wool skirts [...] 

Here’s my recipe for senior stress management: Mix one gorgeous boy with a nice new pair of leather boots, a new cashmere sweater, a long night out, and several drinks. Stir in a very late morning and hot chocolate in bed.

Chuck Bass

Lastly, recall that in book 1, Ziegesar wrote that, due to her alluring looks, Serena was “a full-on groper magnet”; thus, after Cyrus kissed Serena on both cheeks, hugged her a little too tightly, and patted Serena on the hip, Ziegesar penned that Serena didn’t flinch, because she was used to “horny European gropers”. And you may recall from book 1 that after Chuck asked Jenny to introduce him to her breasts, he gyrated his crotch against her ass on the dance floor at The Met, and then Chuck took 14-year-old Jenny into the ladies' room, where he “pulled her dress down so he could get at those massive jugs”. Well, Chuck isn’t mentioned much in book 2, but, unsurprisingly, YA readers learned that he’s up to his old ways. For example, on the dance floor at the wedding reception at the St. Clairel, Chuck promptly groped two Constance schoolgirls: Kati Farkas and Isabel Coates. Ziegesar wrote:

Chuck grabbed both Kati and Isabel’s hands and twirled them away, his hands sliding down their backs to their butts within seconds.

Braless Serena and Sex Machine Blair | GOSSIP GIRL [Book 2] Recap (Part 1)

Gossip Girl: You Know You Love Me (Book 2): Serena and Blair

The original CW Gossip Girl series was called “Mind-blowingly inappropriate.” by the Parents Television Council, “Very bad for you." by the San Diego Union-Tribune, and “A nasty piece of work.” by the New York Post. However, I would argue that the young adult novel series is inarguably more salacious. 

I plan to recap books 1-8, 13, and 14, which were written by Cecily von Ziegesar and are based on Ziegesar's experiences at The Nightingale-Bamford School, an Upper East Side all-girls prep school. 

Serena van der Woodsen

If you’re a fan of the television series, you may be surprised to learn that Serena, a senior at Constance Billard School for Girls, had a small role in Gossip Girl: You Know You Love Me (Book 2). For example, in book 2, Ziegesar further described Serena as having “dark blue eyes”, that Serena’s “pale [“shimmering”] blond hair” had a “golden brilliance”, that Serena’s “pale skin had a pearly sheen from years of using La Mer skin cream”, that Serena “smelled like Chanel No. 5,” and that Serena was prone to wear a “sweater with nothing underneath it.” Consequently, “Serena was like, the coolest senior in New York”.

In addition, readers were reminded about Serena’s wealth and privilege. Ziegesar wrote:

Serena lived with her well-heeled parents […] with a view of the Metropolitan Museum of Art and Central Park. She had a maid and a cook who she could ask to bake her a cake or make her a cappuccino any time she wanted.

Lastly, as for book 2 and Serena, readers were reminded that Serena and Blair’s friendship turned “sour” after Blair learned that Nate, Blair’s boyfriend, had sex, twice in one night, with Serena “nearly two years ago”, which was when Nate and Serena were 16. 

Blair Cornelia Waldorf 

Book 2 began with 16-year-old Blair’s continued quest to lose her virginity to Nate; however, Nate’s goal was to take the virginity of 14-year-old “Jenny, who was in ninth grade at Constance Billard”. Furthermore, as we know, Nate already had sex with Serena, but now, to Blair’s dismay, Nate desired “Jenny [who] was a lowly ninth-grader”. 

Gossip Girl posted that, in preparation for the loss of her virginity, Blair got “a Brazilian wax at the J. Sisters Salon,” because, per Gossip Girl: “After all, no one really wants to go to college a virgin.” 

At Blair’s 17th birthday dinner at Le Giraffe, which was held a whopping three weeks before her actual birthday, 16-year-old “horny” Blair reached under the tablecloth to touch Nate before gulping champagne. Ziegesar wrote:

Blair Waldorf reached under the tablecloth and squeezed Nate’s knee. The candlelight was making her horny. If only Daddy knew what we’re planning to do after this, she thought giddily. She clinked glasses with her father and took a giant gulp of champagne.

Before Nate met Jenny, he was aroused by the idea of seizing Blair’s virginity. Nate observed that Blair looked so hot that she appeared to have already had sex “many times”! Ziegesar wrote:

Nate watched her go. She looked hot in her new black silk halter top, with her straight, dark brown hair hanging between her bare shoulder blades, and her skintight leather pants hugging her hips. She looked like she had already done it, many times. 

Consequently: “Nate was anxious to get back to Blair’s house.” And as for Blair, after some birthday dinner steak and champagne: “She couldn’t wait to get out of there. She couldn’t wait to finally do it [...] Blair seemed impatient, hungrier.”

During the dinner, Blair's father gifted her a pair of MANOLO BLAHNIKs “a pair of beautifully crafted pewter leather mules with adorable little kitten heels,” which she planned to: “wear later that night when she and Nate had sex. Those and nothing else. Thanks, Daddy!”

After the birthday dinner, in her Upper East Side bedroom, Blair undressed in her bathroom, strapped on her “Manolos and spritzed herself with perfume.” (Note: In book 1, before Blair planned to have sex with Nate, Ziegesar wrote that “bad girl” Blair spritzed “once between her legs”.). Blair looked at her reflection in her bathroom’s mirror. “She looked confident and ready.” However: “[...] her breasts [were] so small, but whatever.”

After Blair “pushed open the bathroom door”, Nate found “himself immediately turned on” by Blair's young nude body. Consequently: “The crotch of his red-and-white checked boxers stuck out, tentlike.” 

As for Blair, at the sight of Nate’s erection: “She sucked in her breath.” However, Blair's quest to lose her virginity was thwarted once again. That time by the arrival of her mother and Cyrus, her mother’s fiancé.  Ziegesar wrote: “So much for losing her virginity [...]”

(Note: That was the third time that Blair’s quest to lose her virginity was thwarted. Recall in book 1 that Serena, directly and indirectly, prevented Blair from fulfilling her desires.)

After quickly getting dressed and conversing with her mother and Cyrus, in a page straight out of Restless Virgins: Love, Sex, and Survival in Prep School and American Girls: Social Media and the Secret Lives of Teenagers, Blair asked, “Do you mind if Nate and I go back in my room and watch some TV?” Blair asked.

 

“Of course not. You go right ahead,” her mother said, smiling knowingly at Nate.

Cyrus winked at them. “Nighty-night, Blair,” he said. “Night, Nate.”

Clearly, Blair’s mother and Cyrus knew that Blair didn’t really want to “watch some TV”, and Blair and Nate didn’t disappoint, because as soon as the privileged teens got to Blair’s room, Nate slid his hands under Blair’s Yale sweatshirt: “hoping they’d get back to where they’d left off.” Despite her mother and Cyrus being in the next room, initially, Blair thought that she could “go ahead and have sex and millions of orgasms”; however, in the end, due to her mother’s nearby presence, Blair’s sex drive wilted. Ziegesar wrote:

He pulled her toward him and slid his hands beneath her sweatshirt, hoping they’d get back to where they’d left off. He kissed her neck.

[...] She could go ahead and have sex and millions of orgasms even though her mother and Cyrus were in the next room. She could.

Except she couldn’t. Blair wanted her first time to be perfect, and this was anything but. 

Eleanor, Blair’s mother, and Cyrus planned to have their wedding on the Saturday after Thanksgiving at the (fictional) St. Claire Hotel, which happened to be the same day as Blair’s birthday; thus, naturally, Blair planned to lose her virginity on her mother’s wedding day. Blair’s plan was initiated when she asked her mother, “Can you book a suite for me and my friends?” Ziegesar wrote:

Suddenly Blair had an idea. She and Nate could get a suite! What more perfect place and time to lose your virginity than in a suite at the St. Claire on your seventeenth birthday?

Blair put her fork down, dabbed gently at the corners of her mouth with her napkin, and smiled sweetly at her mother. “Can you book a suite for me and my friends?” she asked.

 

“Of course we can,” Eleanor said. “That’s a fine idea.”

Next, Blair informed Nate that she found the perfect time and place for them to “do it.” Ziegesar wrote:

“[...] my mom and Cyrus are getting suites at the St. Claire for their wedding. And seeing how it’s going to be my birthday and everything, I thought that maybe that would be the perfect time for us to … you know … do it.”

When Blair arrived at her penthouse on Seventy-second Street, “she dropped her backpack on the floor of the foyer. [And] [s]he was greeted by an enormous brown boxer, who trotted up and butted his head into her crotch,” which reminded me of the international bestseller My Secret Garden: Women’s Sexual Fantasies. 

Subsequently, “The door to her mother’s bedroom opened and Cyrus Rose came out, wearing his favorite red silk Versace bathrobe [...] He looked very relaxed. “Hello, Blair!” he shouted, shuffling up and wrapping his arms around her in a bear hug.” However, Blair: “[...] didn’t like standing so close to Cyrus when it was very possible he wasn’t wearing anything under his bathrobe.”

In book 2, Blair had three goals: “finish her senior year at Constance”,  “finally do it with Nate”, and “go to Yale”.

In terms of going to Yale, during the interview at the Ivy with Jason, who was described as “a tall, tanned man with gray hair at his temples and sparkling green eyes”, Blair observed Jason’s derriere, and she performed a kino, a pickup artist seduction technique, before she “earnestly” asked Jason for a promise. Ziegesar wrote:

The interviewer, a tall, tanned man with gray hair at his temples and sparkling green eyes, took her hand and shook it. “So glad to meet you. I’m Jason.” He turned and led Blair into his office. His pants were a little tight in the ass, Blair noticed.

Jason put the cap on his pen and tucked it into his shirt pocket. “Er … do you have any questions for me?”

Blair stopped rubbing her toes and put her foot back on the floor. She scooted her chair forward and reached out to touch Jason’s knee. “If you can promise me to let me in early, I promise to be the best student Yale University has ever had,” she said earnestly. “Can you promise me that, Jason?”

And to cap off the interview, Blair earnestly kissed Jason. Ziegesar wrote:

“I’ll see what I can do,” Jason said. He stood up and held out his hand once more. “Thanks so much for coming in.” He shook Blair’s hand. “Good luck.”

Blair wriggled her feet back into her shoes and smiled winningly at him. “See you next fall,” she said.

And then she stood on tiptoe and kissed him on the cheek.

Ziegesar added that Blair’s: “[...] interviewer definitely wasn’t going to forget that kiss anytime soon.”

In preparation for her, at least, fourth attempt at losing her virginity, Blair was determined, because it was: “[…] her birthday, and tonight she was going to lose it to Nate in that [St. Claire Hotel suite] bed.” Thus, the day before: “[...] she’d been waxed, plucked, exfoliated, steamed, and moisturized from her hair follicles down to her toenails at the Aveda Salon and Spa on Spring Street.” Consequently: “Nate wasn’t going to be able to keep his hands off her tonight.”

In the suite, Blair donned a “Chloé dress [that] fit her body like a condom”, because she was wearing “absolutely nothing underneath” except for a pair of “lace-top stockings”. Consequently, Ziegesar described (17-year-old) Blair as a “bouquet-carrying sex machine”.

After the wedding ceremony, “on the sidewalk on First Avenue, across from the UN,” Blair shared with Nate, “I’m not wearing any underwear.” 

During the wedding reception, which was held “in the elegant ballroom of the St. Claire Hotel”, “Blair tilted forward in her chair and scooped up her champagne flute, downing its contents in one giant gulp.” Why? Because: “[...] she was finally going to lose her virginity to Nate, [and] she wanted to be relaxed.”

However, after bulimic Blair vomited her quenelle, had a smoke, and “spruce[d] herself up”, she discovered Nate: “In the corner [...] kissing a little ninth-grade girl from Constance Billard.”  Ziegesar wrote:

After throwing up her quenelle, Blair had gone outside to smoke a cigarette [...] and headed back to the ladies’ room to spruce herself up.

As soon as she rinsed out her mouth, smoothed down her hair, put on another coat of M•A•C Spice lipstick, and spritzed herself with perfume, she was going to find Nate and take him upstairs to their suite. Enough was enough. It was her birthday and she wanted it her way.

But as she passed through the bar on the way to the ladies’ room, Blair stopped dead. In the corner, Nathaniel Archibald—her Nate—was kissing a little ninth-grade girl from Constance Billard.

Instead of having sex in the suit with Nate, Blair had a sleepover with Serena, where they considered watching pornos and ordering beer, but they watched Breakfast at Tiffany’s. Ziegesar wrote:

Nate and I were supposed to have sex in here tonight,” Blair said, flopping onto the bed in her hotel suite and kicking off her shoes. 

Serena decided not to rub it in by asking Blair what had gone wrong. She pulled her dress off over her head [...] Wearing only her skimpy white satin La Perla underpants, she walked into the bathroom [...] She came out carrying an extra robe for Blair.

Blair took the robe and wriggled out of her dress. “Don’t look,” she warned. “I’m not wearing any underwear.”

Serena walked over to the TV and clicked it on. “I wonder if they get the Playboy channel here. We could watch pornos and order beer from room service,” she joked. She carried the remote over to the bed and sat down.

Breakfast at Tiffany’s was only just getting started.

(Note: In Truman Capote’s Breakfast at Tiffany’s novella, when Holiday Golightly was 13-years-old, she married a [much] older man, when she was barely 15, she lived with a college jock, and when she was 18, she stated, “I can’t get excited by a man until he’s at least forty-two.”) 

Of course, that wasn’t their first sleepover. For instance, and once again from a page out of the international bestseller My Secret Garden: Women’s Sexual Fantasies, during sleepovers, which happened “every weekend”, Blair and Serena took baths together. In addition, they practiced kissing, and they prankcalled their biology teacher. Ziegesar wrote:

When they were younger, Blair and Serena had taken baths together. They’d had sleepovers every weekend, during which they practiced kissing on pillows, made prank calls to their nerdy seventh-grade bio teacher, and stayed up all night giggling. Serena had been there for Blair when she got her period at the end of eighth grade and was terrified of tampons. They’d gotten drunk for the first time together.

Further reading: GOSSIP GIRL [Book 1] Recap (Part 1): Serena

GOSSIP GIRL [Book 1] Recap: “34D” “Slutty Sex Goddess” Jenny Humphrey (Part 3)

Note: In addition to “34D” “Slutty Sex Goddess” Jenny, this recap of Gossip Girl book 1 includes “The Horniest Boy” Chuck Bass, "Huge Slut" Claire and Age-Gap Vanessa

Jenny Humphrey

In Gossip Girl (book 1), Cecily von Ziegesar described Jenny Humphrey, a Constance Billard School for Girls 14-year-old 9th grader, as a “curly-haired” “tiny little freshman” whom “preferred to be invisible.” However, Ziegesar wrote that it would have been easier for Jenny to be invisible: “[...] if her boobs weren’t so incredibly huge. At fourteen, she was a 34D." 

In addition, Ziegesar elaborated that Jenny’s “huge chest” had “[...] boobs that were ten times too big for her body.” Ziegesar wrote:

Over French fries and hot chocolate in a booth at the 3 Guys Coffee Shop [...] Blair looked Ginny [i.e., Jenny Humphrey] up and down. Their cute little ninth-grade helper with the huge chest. She was a total glutton for punishment [....]

Shockingly, in book 1 alone, Ziegesar referred to Jenny’s “boobs” at least nine times. For example, while shopping at Barneys for the Kiss on the Lips benefit at The Met, Jenny salivated over the beautiful dresses, and, naturally, she wanted to “try them all on”; however, Ziegesar wrote that: “When you’re a 34D, you’re kind of limited.”

While perusing the Barneys’ racks, Jenny considered trying on a $600 “purple velvet empire-waist sheath with beaded straps”, but after she “held the dress up to herself. The bodice would barely cover her nipples.”

Ziegesar wrote that even Dan Humphrey, Jenny’s brother, “could not deny” that his sister’s “boobs were really huge.”

Note: The fact that Dan commented on the size of his younger sister's “boobs” isn’t surprising considering that Gossip Girl shared that Dan was “not that innocent”, because he was “up to some kinky shit back at summer camp in eighth grade.” Kinky shit? In the eighth grade? In addition, Dan had a crush on Serena as well. Hence, he fantasized about sneaking Serena into his father’s library, where they would “take each other’s clothes off and kiss on the leather couch in front of the fire.” 

Maureen, a Barneys saleswoman, gave Jenny, despite only being a 9th grader: “all sorts of good advice about support bras and the latest figure enhancing underwear.” Consequently: “Jenny had never been happier.”

Initially, Jenny tried on three dresses, but it was a “disaster”. For example, the first dress got snagged in her bra, the second dress “didn’t even make it over her boobs”, and the third dress “[...] fit, sort of, except it was bright orange”.

Ultimately, Jenny "yanked the orange dress over her head and whipped off her bra, reaching for a black stretch-satin dress [...] Braless, she pulled the dress on over her head and felt it ooze all over her.” Ziegesar wrote that at that moment, Jenny transformed from 14-year-old “little Jenny Humphrey” to “a dangerous, slutty sex goddess”! In addition, Jenny was encouraged to add a pair of “kitten heels, a  thong, and some Chanel Vamp lipstick” [Emphasis added]

Note: The Kiss on the Lips benefit was held by the Constance schoolgirls to raise money for the Central Park Peregrine Foundation. Encouraging gift bags were provided by Kate Spade, which contained “glow-in-the-dark condom[s]”.

At the benefit, Blair observed Jenny: “standing behind her, looking like a human Wonderbra”, but after two flutes of champagne, Jenny wished that “her dress wasn’t so tight.” Subsequently, Jenny was approached by Chuck, “the best-looking boy she’d ever seen” whom asked Jenny to introduce him to her breasts. 

“Well, hello,” a deep voice said, hovering above her head.

“Jenny looked up. Her eyes settled on Chuck Bass’s aftershave-commercial face and she sucked in her breath. He was the best-looking boy she’d ever seen, and he was looking right at her.

“Aren’t you going to introduce me?” Chuck said, staring at Jenny’s chest.

Despite his rakish reputation, it was Blair’s idea that Chuck approach Jenny. Initially, Chuck was “skeptical. But not anymore. The cleavage on her! It was definitely his lucky night.”

When Nate entered The Met, he observed: “Chuck, who was gyrating his crotch against the ass” of Jenny. Unsurprisingly, Nate noted Jenny’s “insane cleavage” and how Chuck held “little Jenny girl so tight it looked like her boobs might explode.” 

As a matter of fact, due to Chuck’s gropings, Jenny had multiple wardrobe malfunctions (i.e., her boobs bounced out of her dress). Ziegesar wrote:

Chuck had his hands full of Jenny Humphrey [...] She was trying to dance as fast as she could, to keep Chuck from groping her, but it was having the opposite effect. Every time she moved her shoulders, her boobs bounced out of her dress and practically hit him in the face.

“Absolutely delighted”, Chuck “put his arms around Jenny’s waist and pulled her close” and guided her into the ladies’ room, where “Jenny opened her mouth and let him thrust his tongue deep into her throat.” 

Note: Jenny “had kissed boys before, [while] playing games at parties.”

Next, Chuck: “pulled her dress down so he could get at those massive jugs”. But before Chuck could go any further, Jenny was saved by Serena and Dan. 

Chuck Bass

Ziegesar described Chuck Bass, a Riverside Prep student, as “aftershave-commercial handsome” and “the horniest boy” in the friend group.

Recall that Chuck Bass, a Riverside Prep student, whom Ziegesar described as “aftershave-commercial handsome”, missed Serena’s lips intentionally “so that his lips landed on her mouth.” However, Serena was unfazed. Later he called Serena, “[...] a perverted slut who made marks on the wall above the bed in your dorm room for every boy you did.” He opined that Serena looked like she had been “thoroughly fucked”. And he wondered if Serena had been a Madam for boarding school sex workers. 

In addition, unsurprisingly, Ziegesar described Chuck as “the horniest boy” in the friend group. So much so that after hiding in the guest room closet, Chuck crawled into bed with Kati Farkas whom was “so drunk she kept throwing up in her sleep”. Shockingly, Kati’s vomit on the sheets didn’t  disturb Chuck, because when it came to schoolgirls “[h]e was completely unshakeable”. Ziegesar wrote:

Chuck Bass, the oldest son of Misty and Bartholomew Bass, was handsome, aftershave-commercial handsome. In fact, he’d starred in a British Drakkar Noir commercial, much to his parents’ public dismay and secret pride. Chuck was also the horniest boy in Blair and Nate’s group of friends. Once, at a party in ninth grade, Chuck had hidden in a guest bedroom closet for two hours, waiting to crawl into bed with Kati Farkas, who was so drunk she kept throwing up in her sleep. Chuck didn’t even mind. He just got in bed with her. He was completely unshakeable when it came to girls.

Naturally, due to coming from old-money, Chuck was not canceled for his schoolboy sexual exploits. Ziegesar wrote:

In other circles, Chuck might have been banished as a slimeball of the highest order, but these families had been friends for generations. Chuck was a Bass, and so they were stuck with him.

And no telling when Chuck’s carnal exploits began, because (possibly) since the first grade, he desired to “sleep” with girls, including Serena. Ziegesar wrote:

All four of them looked at Serena, who was still chatting happily with Nate. Chuck saw the girl he’d wanted to sleep with since he could remember wanting to sleep with girls—first grade, maybe?

Lastly, Chuck photographed the bawdy after-school gatherings in his suite, and recall that he kept the photographs on the coffee table. Besides the photographs of the nude prep schoolers in the hot tub, Chuck had a photograph of “Blair wearing only her underwear, jumping up and down on the bed [of the suite] with a magnum of champagne in her hand.”

Claire and the L’Ecole Schoolgirls

Ziegesar described Claire, a student at L’Ecole, an Upper East Side French prep school, as a “huge slut” and the L’Ecole schoolgirls as the “ho’s of the Upper East Side school system”. Why? Well, Claire and the “L’Ecole girls all wear really tight clothes and short skirts and high heels.” And readers can infer that, like Jenny, Claire’s “boobs were really huge,” because, once “Claire laugh[ed] so hard her boobs nearly pop[ped] out of her shirt”. Gossip Girl posted:

There’s usually a group of kids from L’Ecole standing around outside the pizza place, so N [i.e., Nate] will stop and flirt with this one girl who I’ll call Claire, who acts all shy and pretends she doesn’t speak English, but she’s actually really bad at French and a huge slut.

N has this cute little gag where he buys two slices and he always offers Claire one. She holds onto it the whole time they’re talking and finally takes a little weeny bit off the tip of the slice. Then N goes, “I can’t believe you did that, you’re eating my pizza!” and swipes the thing out of her hands and eats the whole thing in like two bites. This makes Claire laugh so hard her boobs nearly pop out of her shirt. The L’Ecole girls all wear really tight clothes and short skirts and high heels. They’re like, the ho’s of the Upper East Side school system.

When one considers salacious Serena and bawdy Blair, Ziegesar’s description of the L’Ecole schoolgirls as the “ho’s of the Upper East Side school system” seems a bit biased. 

Vanessa Abrams

Vanessa Abrams, another Constance schoolgirl, initially wanted: “only one thing in life: to go to NYU and major in film.” However, after she went to a bar to see SugarDaddy, her sister’s band, Vanessa wanted Clark, the bartender. [Emphasis added] 

Clark, whom Ziegesar described as in his: “[...] twenties, with red hair, long sideburns, and a cute, sly smile,” informed (approximately) 16-year-old Vanessa that he had a secret crush on her, and he prepared Vanessa a Kiss Me before they shared an age-gap kiss. 

“Can I tell you a secret?” Clark said. He poured a few different things into a martini shaker and shook it up. 

“What?” she said.

“[...] I’ve kind of had a crush on you since I first saw you.”

Vanessa stared at him. Was he joking?

Clark poured the drink out of the martini shaker into a short little glass [...]

“What’s it called?” she said.

“Kiss me,” Clark said, with an absolutely straight face.

Vanessa put the drink down and leaned over the bar [...] She was about to be kissed.

Almost immediately after their first kiss, “She couldn’t wait to kiss him again”. Subsequently, Gossip Girl posted that the age-gap couple was watching rented horror movies at Clark’s apartment in Brooklyn. However, it appears that Vanessa and the bartender did not have sex, because Gossip Girl asked encouragingly: “Will she and that bartender get it on?”

GOSSIP GIRL [Book 1] Recap: “Nasty, Slutty” Serena (Part 1)

GOSSIP GIRL [Book 1] Recap: “Sex Kitten” Blair Waldorf (Part 2)